The agency’s first location is a small second floor office at 1224 St. Clair Avenue West, Toronto. They later move to 1710 Dufferin Street in 1970 and then 1055 Wilson Avenue in 1973. One of the first employees of Ciccolini Insurance Agency, Josie Bertucci, exemplifying dedication and true loyalty, continues to work with Masters today.

1972

Max Ciccolini leaves a teaching position with the Toronto Board of Education to join his two brothers to oversee the administration and finances of their growing insurance agency.

1981

After sustaining modest growth in the late 70's, the Ciccolini brothers welcome Gary Corby to the partnership. With Gary's wealth of knowledge and experience in the surety bond industry, the agency begins to focus on building a real construction-oriented commercial book of business. Soon after, the partners decide to change the agency name and operate under Masters Insurance Limited. Through a tenacious work ethic and passion for servicing the insurance needs of the construction industry, Masters quickly becomes a well respected leader in this field.

1984

After graduating from York University, Rita Ciccolini joins Masters to expand the Personal Lines division of the brokerage. In 1995, she takes a two-year leave as a Minister's Chief of Staff at Queen's Park. Rita then returns to the business to head up the Group Benefits division of Masters Life Insurance Agency Ltd.

1986

Frank Ciccolini Jr. is a graduate of St Michael's College School, and the University of Toronto’s Bachelor of Commerce program. After mentoring at a global financial institution, he joins Masters as a Life Insurance and Group Benefits specialist and then licenses Masters Financial to expand into money management.

Masters Life Insurance Agency Ltd. officially launches focusing on Life Insurance as well as Personal and Group Benefits.

1987

After graduating from Virginia Tech University where he attended university on a full golf scholarship, Doug Corby spends three years playing professionally before joining the brokerage on a full time basis. Doug is presently a senior member of Masters’ Surety Bond department and oversees day to day operations in Masters Hamilton.

After attending Michael Power St. Joseph's High School and York University for its Math for Commerce program, Cathy Ciccolini permanently joins Masters and is an integral part of the Commercial Lines department. She also holds a designation of CIP - Chartered Insurance Professional.

1988

After 22 years, Masters grows to 55 employees.

1989

Masters Insurance opens its second office in Hamilton, Ontario.

After graduating from Michigan State University, Wade Corby joins his father Gary to foster and build the Surety Bond department in the Toronto office.

1993

Mark Corby graduates from Virginia Tech University. A short while later, he begins work at Masters’ Hamilton office, joining his brother Doug. He now heads up the Hamilton Commercial Lines department.

1994

After graduating from St. Michael's College School and earning a Bachelor of Commerce degree from the University of Toronto, Patrick Ciccolini joins Masters Financial. After 3 years of accumulating in-house experience in portfolio construction and insurance planning strategies, Patrick begins his role as investment and insurance advisor, specializing in strategies for personal and corporate planning.

1996

Masters Insurance opens its third office in Windsor, Ontario.

Michael Ciccolini graduates from the University of Western Ontario with a Bachelor of Arts and Political Science. He joins a large insurance company as a career trainee to learn all facets of the insurance industry, then bringing his acquired knowledge to Masters. Michael also carries his designation of CIP - Chartered Insurance Professional, graduating with Honours, and is a key member of the Toronto office's Commercial department.

1998

After 32 years, Masters grows to 75 employees.

1999

Sam Ciccolini receives the Order of Ontario in acknowledgement of his charitable endeavours and community involvement.

2001

After graduating from St. Michael's College School and then earning his BBA degree from York University’s Schulich School of Business, Robert Ciccolini joins the family brokerage and now helps lead the Commercial Insurance team.

2004

Anthony Ciccolini graduates from St. Michael's College School and goes on to earn his BBA degree from York University’s Schulich School of Business, where he specialized in finance. He joins Masters Insurance and currently plays an essential role within the Commercial department.

2005

Masters Insurance opens its fourth office in Ottawa, Ontario.

2006

In recognition of his service and dedication to his community, Sam Ciccolini receives the Order of Canada.

2011

Masters celebrates its 45th anniversary.

2016

For generations, Masters Insurance Limited will continue its pursuit of being recognized as one of Canada's most respected insurance brokerages, offering professional services and expert advice, deeply rooted in core principles and family values.